Hiring Your First Employees as a Solo Entrepreneur
- Alex Flaugher
- 1 day ago
- 6 min read
Picture a founder two years into building something real.
It started at a kitchen table. Now there are actual clients, actual revenue, and a calendar booked out further than they ever imagined.
For a long time, that founder was the whole operation. Every email, every deal, every problem, they handled it themselves, because nobody else existed yet to hand it to.
For a while, that's not a warning sign. That's just what building something looks like early on.
Then the business keeps growing, and something shifts.
A referral comes in for a project that would've been a dream client a year ago, and the founder has to say no. Not because the work isn't good. Because there's no room left in the week.
It happens again a few months later. Then it becomes a pattern, good opportunities quietly turned away, because the person who built the business is now the ceiling on how big it can get.
That's usually the moment a founder finally asks: do I need to hire someone?
It's a fair question, and a loaded one, with a lot more to it than yes or no. Let's get into it.
Here's Hiring Your First Employees as a Solo Entrepreneur.
Step 1: Figuring out if you're actually ready
Why "I'm Overwhelmed" Isn't the Right Reason
A lot of founders treat their first hire like a finish line. Get through the hard part solo, then reward yourself with help.
It's backwards. The hire is what unlocks the next stage of growth, not a prize for surviving the last one.
I've watched founders put off hiring for a year, run themselves into the ground, and then bring someone on out of desperation instead of strategy.
That's a rushed decision dressed up as a smart one, and it usually shows.
The good news is there's a way to catch this before it happens, if you know what to actually watch for.
The Signals Worth Paying Attention To
The clearest one is money you're leaving on the table.
You're saying no to clients or projects simply because there's no time left in the week.
You're spending hours on work that pays far less than your time is actually worth.
Deadlines are slipping, and the honest answer is that you're the reason why.
Any one of those is a sign you need more hands. All three together means you needed them a while ago.
That said, wanting help and being able to afford it aren't the same thing. If your revenue can't comfortably carry a salary for a full year, it's not time yet, even if the exhaustion says otherwise.
The founders who get this right are honest with themselves about which one they're actually feeling.
As Financial Advisors for Business Owners, we have experience navigating these type of questions.
What To Hire For First
Most founders default to hiring someone who reminds them of themselves. Someone who "gets it" the way they do.
I understand the instinct. It's still usually the wrong call.
Try splitting your business into three categories instead.
The stuff only you can do: the vision, the key relationships, the calls that carry real risk.
The stuff you're good at but shouldn't be doing anymore: delivery, execution, the daily grind of the work itself.
The stuff you're bad at and have been avoiding: admin, invoicing, scheduling, the follow-up that never happens.
Founders tend to hire into the first bucket when they should be hiring into the second and third.
Your first employee should be filling in your gaps, not mirroring your strengths.
That's how you end up with a business that gets stronger with each hire, instead of just louder.
Step 2: Actually Making the Hire
What An Employee Really Costs You
Founders almost always budget for the salary line and stop there.
That's not the real number.
Payroll taxes, workers' comp, unemployment insurance, benefits, tools, and the time you'll spend training someone all stack on top of it.
A fair estimate is 1.25 to 1.4 times the salary once everything is accounted for.
If your business can't comfortably absorb that fully loaded number, the answer isn't to skip the math. It's to either adjust the offer or wait a little longer.
This is one of the first things we sit down and run through with founders before they ever extend an offer.
Contractor, Part-Time, or Full-Time
How you structure the hire matters just as much as who you pick.
Going straight to a full-time employee is the biggest commitment and the biggest risk you can take on.
For most first-timers, it's smarter to test the role before you commit to it permanently.
Contract or fractional help lets you prove the role needs to exist before you build a full-time position around it.
Part-time makes sense when the need is real, but not yet a 40-hour-a-week need.
Full-time is the right call once the workload and the budget have both proven themselves out.
There's no bonus points for jumping straight to the biggest commitment. Getting the structure right matters more than getting there fast.
Write the Job Down Before You Post It
Without a documented process, your new hire spends their first months just asking you questions instead of doing the work.
This is the step I see skipped most, and it's the one that costs founders the most later.
Write out what the role owns. Write out what a strong week looks like in that seat. Write out the tools and systems they'll actually use day to day.
Do that work up front, and you're handing someone a real job. Skip it, and you're handing them a puzzle to solve on your dime.
Step 3: Keeping Them Around
The First 90 Days Decide More than the Hire Does
This is the part founders think about the least, and it might matter more than anything above it.
Picture this. You make a great hire. They show up ready to go. And three weeks in, they still can't tell you what success in the role even looks like.
Without a clear target, even a genuinely talented hire starts to drift.
Founders who keep their first employees are the ones who treat the first three months as a real plan, not just a formality before the "real" job starts.
That means a written 30-60-90 day roadmap, consistent check-ins, and a concrete outcome they're working toward, not a job description they got handed once and never revisited.
The Boring Legal Stuff You Can't Skip
None of this is exciting, but skipping it doesn't make it go away.
An EIN and the right state payroll registration.
Workers' compensation coverage in place.
A real, signed employment agreement.
A written job description that actually reflects the role.
Skipping these steps doesn't save you time now. It just pushes the cost down the road, where it's more expensive and harder to untangle.
Final Thought
If you're a solo entrepreneur weighing your first hire, here's the question I'd actually ask you.
Are you hiring because you're the bottleneck, or because you're just tired?
If you can't answer that cleanly, it's worth talking through before you make the leap.
Get the structure right early, and you save yourself from a lot of expensive corrections down the line.
That's the kind of planning we do alongside founders every day at Moment Private Wealth, building the business and the personal financial picture together, so decisions like this one move you forward instead of creating something to clean up later.
If you are a business owner who is looking at hiring your first employee or wondering the best way to structure your business, schedule a call, and talk with a Moment founder.
For more on how we are working with Entrpreneurs check out "Entrepreneurship Explained: Quick Wins or Long-Term Wealth?"
Get in Touch With An Advisor
Frequently Asked Questions
Here are some answers to questions I received frequently about this topic.
How do I know if I'm actually ready to hire my first employee?
Look at what you're turning down, not just how tired you feel. If you're declining work, delaying projects, or spending your time on tasks well below your value, that's your answer. Exhaustion isn't the same signal as readiness. Your revenue also needs to be able to carry the cost for a full year, not just the first few months.
Should my first hire be full-time or a contractor?
For most first-time founders, starting with a contractor or fractional hire is the safer move. It gives you a chance to confirm the role is actually necessary before you commit to the ongoing costs of a full-time employee.
What does an employee actually cost beyond their salary?
Budget for roughly 1.25 to 1.4 times the salary once you factor in payroll taxes, workers' comp, unemployment insurance, benefits, and the tools they'll need. Founders who only plan for the salary number are almost always caught off guard later.
What's the biggest mistake founders make with their first hire?
Hiring someone who works just like them, instead of someone who covers what they're weak at. Your first hire should expand what the business can do, not repeat what you already do well.
Can Moment Private Wealth help me think through the financial side of hiring?
Yes. Understanding the true cost of a hire, how it impacts your income, and how it fits into your broader financial plan is exactly the kind of work we do alongside founders.
*Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.
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